Pyridone dyes containing a oxydiazone substituent

ABSTRACT

Compounds of the general formula I ##STR1## where R is hydrogen or an aliphatic, alkenyl, cycloaliphatic, araliphatic, aromatic or heteroaromatic radical, R 1  is hydrogen, amino, hydroxyl or C 1  -C 3  -alkyl, R 2  is hydrogen, unsubstituted or substituted alkyl, allyl, aralkyl or aryl or alkylamino or arylamino, X is hydrogen, chlorine, bromine, nitro, methyl, phenoxy, tolyloxy, dimethylphenoxy, chlorophenoxy or C 1  -C 8  -alkoxy, Y is hydrogen, chlorine or bromine, and Z is hydrogen, acetyl, carbamyl or cyano, are useful for dyeing and/or printing textile material.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to compounds of the general formula I ##STR2## where R is hydrogen or an aliphatic, alkenyl, cycloaliphatic, araliphatic, aromatic or heteroaromatic radical, R¹ is hydrogen, amino, hydroxyl or C₁ -C₃ -alkyl, R² is hydrogen, unsubstituted or substituted alkyl, allyl, aralkyl or aryl or alkylamino or arylamino, X is hydrogen, chlorine, bromine, nitro, methyl, phenoxy, tolyloxy, dimethylphenoxy, chlorophenoxy or C₁ -C₈ -alkoxy, Y is hydrogen, chlorine or bromine, and Z is hydrogen, acetyl, carbamyl or cyano.

2. Description of the Prior Art:

R is, for example, C₁ -C₁₇ -alkyl which can furthermore be interrupted by oxygen and substituted by, for example, phenyl, methylphenyl, carboxyl, a carboxylic ester group or unsubstituted or substituted phenoxy, or R is hydroxycarbonylvinyl, alkoxycarbonylvinyl, cycloalkyl of 5 to 7 carbon atoms, phenyl which is unsubstituted or substituted by chlorine, bromine, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, or pyridyl or thienyl.

Specific examples of radicals R are methyl, ethyl, n- and i-propyl, n- and i-butyl, n- and i-pentyl, n-hexyl, n-heptyl, 1-ethylpentyl, decyl, undecyl, dodecyl, C₁₅ H₃₁, C₁₇ H₃₅, H₅ C₂ O₂ CC₂ H₄ --, H₉ C₄ O₂ CC₂ H₄ --, ##STR3## H₃ COC₂ H₄ O₂ CC₂ H₄, H₅ C₂ OC₂ H₄ O₂ CC₂ H₄, H₉ C₂ H₄ O₂ CC₂ H₄, 2-ethylhexyloxymethyl and -ethyl, hexyloxyethyl, isopropoxyethyl, phenyl, chlorophenyl, cyclohexyl and in particular phenoxymethyl and -ethyl and benzyloxymethyl.

Alkyl radicals R² are in particular, of not more than 18 carbon atoms, and can be straight-chain or branched. Phenyl-C₁ -C₄ -alkyl and unsubstituted or substituted phenyl or phenylamino are also suitable.

Specific examples of radicals R² are methyl, ethyl, n- and i-propyl, n- and i-butyl, n-pentyl, n-hexyl, n- and i-heptyl, n- and i-octyl, n-nonyl, n-decyl, n-undecyl, phenyl, m-tolyl, p-tolyl, phenylamino, 2-ethylhexyloxypropyl, hexyloxypropyl, hydroxyethoxyethyl and hydroxybutoxypropyl.

Examples of alkoxy radicals X are octyloxy, β-ethylhexyloxy, hexyloxy, phenoxy, amyloxy, butoxy, i-butoxy, propoxy, i-propoxy, ethoxy and, preferably, methoxy.

To prepare the compounds of the formula I, a diazonium compound of an amine of the formula ##STR4## can be reacted with a coupling component of the formula ##STR5## In the Examples which follow, and illustrate the preparation, parts and percentages are by weight, unless stated otherwise.

Of particular importance are compounds of the formula Ia ##STR6## where R is C₃ -C₁₇ -alkyl, or is C₁ - or C₂ -alkyl which is substituted by C₄ -C₈ -alkoxy, phenoxy or benzyloxy, or is C₁ -C₄ alkyl which is substituted by C₁ -C₈ -alkoxycarbonyl which may or may not be interrupted by oxygen, and R² is hydrogen, C₁ -C₆ -alkyl or allyl, and R² is not hydrogen when R contains a phenyl ring. Preferably the sum of the carbon atoms of R and R² together is from 4 to 13, in particular from 5 to 11.

If R² is hydrogen, R should preferably not contain a phenyl ring.

The compounds of the formula I are yellow disperse dyes which have very good fastness properties and excellent color strength. Moreover, the tinctorial properties are generally satisfactory.

Dyes which contain hydroxyl groups in R or R² are, as a rule, suitable for leather and nylon.

Some of the dyes are also useful for printing on cotton and cotton/polyester blends, for example by the method described in German Patent No. 1,811,796.

The stated λ_(max) values for the dyes were determined in a solution comprising 9 parts of dimethylformamide and 1 part of glacial acetic acid.

EXAMPLES 1

98 parts of the compound of the formula ##STR7## are dissolved in 250 parts by volume of 96-98% strength sulfuric acid at from 0° to 20° C., 25 parts by volume of a 98% strength nitric acid are added at from 10° to 40° C., while cooling, the mixture is stirred overnight at room temperature and then poured onto about 900 parts of ice and 300 parts of water at 0° C., and stirring is then continued to complete the reaction. The resulting precipitate of the product of the formula ##STR8## is filtered off under suction, washed neutral with water, and dried to give 116 parts of a colorless powder having a melting point of 110° C.

210 parts of this product in 500 parts by volume of alcohol and 900 parts by volume of 25% strength ammonia water are stirred in an autoclave for 10 hours at 150° C.

Thereafter, the solvent is distilled off as far as possible, and water is added to the residue to precipitate the product. The latter is filtered off under suction and dried, and 193 parts of the diazo component of the formula ##STR9## are obtained. 44 parts of this diazo component are stirred with 210 parts by volume of glacial acetic acid, about 60 parts of bromine are then added dropwise at from 25° to 55° C., and at the same time about 80 parts of sodium acetate are added.

After the bromination, the mixture is poured into water, and the pH is brought to 4-6 with sodium hydroxide solution. The product is filtered off under suction, washed with water and dried to give 56 parts of a yellow powder of the formula ##STR10## which has a melting point of 152° C.

13.5 parts of the bromine-free product are suspended in 80 parts by volume of glacial acetic acid, 20 parts by volume of propionic acid and 3 parts of sulfuric acid, 22 parts of a 44% strength solution of nitrosylsulfuric acid are added dropwise in the course of 20 minutes at from 0° to 7° C., and the mixture is then stirred for a further 2-3 hours at from 0° to 5° C. The clear solution is then poured onto about 180 parts of ice and 150 parts of water at 0° C., and excess nitrous acid is destroyed in a conventional manner. The pH of the solution is then increased to 1.0-1.5 by adding a little sodium acetate, the temperature being kept at 0° C. by adding ice.

A solution of 14.5 parts of 1-n-hexyl-2-hydroxy-3-cyano-4-methylpyrid-6-one in 200 parts of water and 10 parts of 50% strength sodium hydroxide solution are run into the resulting diazonium salt solution, while stirring thoroughly, the temperature being kept at 0°-10° C. by adding ice water. A yellow precipitate of the dye of the formula ##STR11## is obtained.

Filtration under suction, washing with water and drying in a conventional manner give 24.4 parts of a yellow powder which dissolves in dimethylformamide to give a yellow solution. The dye dyes polyester fabric in very lightfast intense hues, and has very good tinctorial properties. A solution of the dye in a 9:1 mixture of acetonitrile with glacial acetic acid has an absorption maximum at 442 nm (concentration about 0.01 part/1,000 parts by volume).

For example, the intermediates of the general formula II which are listed in Table A can be prepared by a procedure similar to that described in Example 1.

                  TABLE A                                                          ______________________________________                                          ##STR12##                     II                                                                                λ.sub.max ·                                                            Melting                                                                (mm,in  point                                No.  R            X      Y   Z    CH.sub.3 OH)                                                                           °C.                           ______________________________________                                          1   CH.sub.3     H      Cl  Cl           108                                   2   CH.sub.3     NO.sub.2                                                                              Cl  Cl            93                                   3   CH.sub.3     NO.sub.2                                                                              Br  NH.sub.2     150-153                               4   CH.sub.3     NO.sub.2                                                                              Cl  NH.sub.2     95-97                                 5   C.sub.2 H.sub.5                                                                             NO.sub.2                                                                              H   NH.sub.2     123-125                               6   C.sub.2 H.sub.5                                                                             NO.sub.2                                                                              Cl  NH.sub.2                                                                            402                                           7   C.sub.2 H.sub.5                                                                             NO.sub.2                                                                              Br  NH.sub.2     127-129                               8   C.sub.2 H.sub.5                                                                             H      H   Cl           16-20                                 9   C.sub.2 H.sub.5                                                                             NO.sub.2                                                                              H   Cl           45-49                                10   C.sub. 3 H.sub.7                                                                            H      H   Cl           57-58                                11   C.sub.3 H.sub.7                                                                             NO.sub.2                                                                              H   Cl           36-40                                12   C.sub.3 H.sub.7                                                                             NO.sub.2                                                                              H   NH.sub.2     128-131                              13   C.sub.3 H.sub.7                                                                             NO.sub.2                                                                              Cl  NH.sub.2                                                                            403                                          14   C.sub.3 H.sub.7                                                                             NO.sub.2                                                                              Br  NH.sub.2     85-87                                15   (CH.sub.3).sub.2 CH                                                                         H      H   Cl           <25                                  16   (CH.sub.3).sub.2 CH                                                                         NO.sub.2                                                                              H   Cl           30-33                                17   (CH.sub.3).sub.2 CH                                                                         NO.sub.2                                                                              Cl  NH.sub.2                                                                            403                                          18   (CH.sub.3).sub.2 CH                                                                         NO.sub.2                                                                              Br  NH.sub.2                                                                            403                                          19                                                                                   ##STR13##   H      H   Cl           10-20                                20                                                                                   ##STR14##   NO.sub.2                                                                              H   Cl   304     20-26                                21                                                                                   ##STR15##   NO.sub.2                                                                              H   NH.sub.2     60-66                                22                                                                                   ##STR16##   NO.sub.2                                                                              Cl  NH.sub.2                                                                            403.5                                        23                                                                                   ##STR17##   NO.sub.2                                                                              Br  NH.sub.2                                                                            403.5                                        24   n-C.sub.5 H.sub.11                                                                          H      H   Cl   246                                          25   n-C.sub.5 H.sub.11                                                                          NO.sub.2                                                                              H   Cl   306                                          26   n-C.sub.5 H.sub.11                                                                          NO.sub.2                                                                              H   NH.sub.2                                                                            405                                          27   n-C.sub.5 H.sub.11                                                                          NO.sub.2                                                                              Cl  NH.sub.2                                                                            403                                          28   n-C.sub.5 H.sub.11                                                                          NO.sub.2                                                                              Br  NH.sub.2                                                                            403                                          29   (CH.sub.3).sub.3 C                                                                          H      H   Cl   246.5   0-5                                  30   (CH.sub.3).sub.3 C                                                                          NO.sub.2                                                                              H   Cl   303     103                                  31   (CH.sub.3).sub.3 C                                                                          NO.sub.2                                                                              H   NH.sub.2                                                                            406.5   133-135                              32   (CH.sub.3).sub.3 C                                                                          NO.sub.2                                                                              Cl  NH.sub.2     134-136                              33   (CH.sub.3).sub.3 C                                                                          NO.sub.2                                                                              Br  NH.sub.2                                                                            402.5   135-137                              34   n-C.sub.6 H.sub.13                                                                          H      H   Cl   246                                          35   n-C.sub.6 H.sub.13                                                                          NO.sub.2                                                                              H   Cl   307                                          36   n-C.sub.6 H.sub.13                                                                          NO.sub.2                                                                              H   NH.sub.2                                                                            407                                          37   n-C.sub.6 H.sub.13                                                                          NO.sub.2                                                                              Cl  NH.sub.2                                                                            404.5                                        38   n-C.sub.6 H.sub.13                                                                          NO.sub.2                                                                              Br  NH.sub.2                                                                            404.5                                        39   CH.sub.3 OCH.sub.2 CH.sub.2                                                                 NO.sub.2                                                                              H   NH.sub.2     137-141                              40   CH.sub.3 OCH.sub.2 CH.sub.2                                                                 NO.sub.2                                                                              Br  NH.sub.2                                                                            401.5                                        41   n-C.sub.7 H.sub.15                                                                          H      H   Cl   247                                          42   n-C.sub.7 H.sub.15                                                                          NO.sub.2                                                                              H   Cl   305                                          43   n-C.sub.7 H.sub.15                                                                          NO.sub.2                                                                              H   NH.sub.2                                                                            407                                          44   n-C.sub.7 H.sub.15                                                                          NO.sub.2                                                                              Cl  NH.sub.2                                                                            406                                          45   n-C.sub.7 H.sub.15                                                                          NO.sub.2                                                                              Br  NH.sub.2                                                                            406                                          46                                                                                   ##STR18##   H      H   Cl           <10                                  47                                                                                   ##STR19##   NO.sub.2                                                                              H   Cl   304     ≦16                           48                                                                                   ##STR20##   NO.sub.2                                                                              H   NH.sub.2                                                                            405.5                                        49                                                                                   ##STR21##   NO.sub.2                                                                              Cl  NH.sub.2                                                                            404                                          50                                                                                   ##STR22##   NO.sub.2                                                                              Br  NH.sub.2                                                                            405                                          51   (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                          H      H   Cl   245                                          52   (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                          NO.sub.2                                                                              H   Cl   307                                          53   (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                          NO.sub.2                                                                              H   NH.sub.2                                                                            405                                          54   (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                          NO.sub.2                                                                              Cl  NH.sub.2                                                                            406                                          55   (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                          NO.sub.2                                                                              Br  NH.sub.2                                                                            406                                          56   CH.sub.3 (CH.sub.2).sub.10                                                                  H      H   Cl   246                                          57   CH.sub.3 (CH.sub.2).sub.10                                                                  NO.sub.2                                                                              H   Cl   306                                          58   CH.sub.3 (CH.sub.2).sub.10                                                                  NO.sub.2                                                                              H   NH.sub.2                                                                            407                                          59   CH.sub.3 (CH.sub.2).sub.10                                                                  NO.sub.2                                                                              Cl  NH.sub.2                                                                            406                                          60   CH.sub.3 (CH.sub.2).sub.10                                                                  NO.sub.2                                                                              Br  NH.sub.2                                                                            406                                          61   CH.sub.3 (CH.sub.2).sub.14                                                                  H      H   Cl   247                                          62   CH.sub.3 (CH.sub.2).sub.14                                                                  NO.sub.2                                                                              H   Cl   306                                          63   CH.sub.3 (CH.sub.2).sub.14                                                                  NO.sub.2                                                                              H   NH.sub.2                                                                            407                                          64   CH.sub.3 (CH.sub.2).sub.14                                                                  NO.sub.2                                                                              Cl  NH.sub.2                                                                            406                                          65   CH.sub.3 (CH.sub.2).sub.14                                                                  NO.sub.2                                                                              Br  NH.sub.2                                                                            406                                          66   CH.sub.3 (CH.sub.2).sub.16                                                                  H      H   Cl   247                                          67   CH.sub.3 (CH.sub.2).sub.16                                                                  NO.sub.2                                                                              H   Cl   307                                          68   CH.sub.3 (CH.sub.2).sub.16                                                                  NO.sub.2                                                                              H   NH.sub.2                                                                            407                                          69   CH.sub.3 (CH.sub.2).sub.16                                                                  NO.sub.2                                                                              Cl  NH.sub.2                                                                            406                                          70   CH.sub.3 (CH.sub.2).sub.16                                                                  NO.sub.2                                                                              Br  NH.sub.2                                                                            406                                          71   CH.sub.3 OCH.sub.2                                                                          H      H   Cl           66-70                                72   CH.sub.3 OCH.sub.2                                                                          NO.sub.2                                                                              H   Cl   303                                          73   CH.sub.3 OCH.sub.2                                                                          NO.sub.2                                                                              H   NH.sub.2                                                                            405                                          74   CH.sub.3 OCH.sub.2                                                                          NO.sub.2                                                                              Cl  NH.sub.2                                                                            401                                          75   CH.sub.3 OCH.sub.2                                                                          NO.sub.2                                                                              Br  H    401                                          76   C.sub.2 H.sub.5 OCH.sub.2                                                                   H      H   Cl           64-67                                77   C.sub.2 H.sub.5 OCH.sub.2                                                                   NO.sub.2                                                                              H   Cl   303                                          78   C.sub.2 H.sub.5 OCH.sub.2                                                                   NO.sub.2                                                                              H   NH.sub.2                                                                            406                                          79   C.sub.2 H.sub.5 OCH.sub.2                                                                   NO.sub.2                                                                              Cl  NH.sub.2                                                                            401                                          80   C.sub.2 H.sub.5 OCH.sub.2                                                                   NO.sub.2                                                                              Br  NH.sub.2                                                                            401                                          81   C.sub.3 H.sub.7OCH.sub.2                                                                    H      H   Cl           33-38                                82   C.sub.6 H.sub.5                                                                             H      H   Cl           115                                  83   C.sub.6 H.sub.5                                                                             NO.sub.2                                                                              H   Cl   245.5                                        ______________________________________                                    

EXAMPLE 2

240 parts of 3-acetylaminobenzonitrile in a mixture of 450 parts by volume of water, 87 parts of sodium carbonate, 129 parts of hydroxylamine sulfate and 450 parts by volume of isobutanol, and 2 parts of a compound which forms a complex with heavy metals (eg. ethylenediaminetetraacetic acid), are stirred for 6 hours, with vapor cooling, after which the lower, aqueous phase is cooled and then separated off, and 450 parts by volume of distilled water are added. 270 parts of 2-ethylhexanoyl chloride and sodium carbonate are then added, while stirring very thoroughly, so that the mixture is kept at pH 4-7, and stirring is then continued for a further 30 minutes. The mixture is then diluted with water, and the resulting precipitate is filtered off under suction, washed with water and dried to give 420 parts of the compound of the formula ##STR23## of melting point 148° C.

If the product obtained is heated at 150°-160° C., and the melt is stirred for 1 hour at this temperature, water is eliminated to give the compound of the formula ##STR24## in the form of a viscous oil which, after standing for a relatively long time, crystallizes to give a product of melting point 88°-90° C. Yield: 380 parts.

75 parts of this oil in 250 parts by volume of methanol are stirred with 50 parts of concentrated sulfuric acid for from 2 to 21/2 hours, with vapor cooling. Thereafter, some of the methanol is distilled off, precipitation is effected by pouring the mixture onto ice water, and the pH is increased to 5-7. The oily phase is extracted with cyclohexane, ethyl acetate, etc., and the product of the formula ##STR25## is isolated in a conventional manner.

64 parts of a very slightly yellowish oil, whose UV spectrum in methanol has a maximum at 318 nm, are obtained.

For example, the intermediates of the formula III which are shown in Table B can be obtained by a procedure similar to that described in Examples 1 and 2.

                                      TABLE B                                      __________________________________________________________________________      ##STR26##                                     III                                                                      λ.sub.max (nm)                                                          or melting                            No.                                                                               R                     X       Z       point (°C.)                    __________________________________________________________________________     1  CH.sub.3              H       NHCOCH.sub.3                                                                           170-173                               2  CH.sub.3              NHCOCH.sub.3                                                                           H        90-92                                3  CH.sub.3              Cl      Cl      108-111                               4  C.sub.2 H.sub.5       H       NHCOC.sub.2 H.sub.5                                                                    148-150                               5  C.sub.2 H.sub.5       NHCOCH.sub.3                                                                           H       131                                   6  C.sub.3 H.sub.7       NHCOCH.sub.3                                                                           H       295.5 nm                              7  C.sub.3 H.sub.7       H       NHCOCH.sub.3                                                                           136                                   8  HO.sub.2 CC.sub.2 H.sub.4                                                                            NHCOCH.sub.3    154                                   9  n-C.sub.4 H.sub.9     NHCOCH.sub.3                                                                           NHCOCH.sub.3                                                                           276.5 nm                              10 t-C.sub.4 H.sub.9     NHCOCH.sub.3                                                                           NHCOCH.sub.3                                                                           170-172                               11 CH.sub.2 OC.sub.6 H.sub.5                                                                            NHCOCH.sub.3                                                                           H       108-110                               12 n-C.sub.4 H.sub.9     NHCOCH.sub.3                                                                           H       156-160                               13 n-C.sub.6 H.sub.13    H       NHCHO   153-157                               14 n-C.sub.6 H.sub.13    H       NHCOCH.sub.3                                                                           272 nm                                15                                                                                 ##STR27##            H       NHCOCH.sub.3                                                                           158-163                               16 n-C.sub.7 H.sub.15    NHCOCH.sub.3                                                                           H       144-145                               17 n-C.sub.8 H.sub.17    NHCOCH.sub.3                                                                           H       141-144                               18 n-C.sub.8 H.sub.17    H       NHCOCH.sub.3                                                                           274 nm                                19 (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                                   NHCOCH.sub.3                                                                           H       135-140                               20 n-C.sub.11 H.sub.23   NHCOCH.sub.3                                                                           H       237-241                               21 n-C.sub.11 H.sub.23   H       NHCOCH.sub.3                                                                           273 nm                                22 CH.sub.3 (CH.sub.2).sub.12                                                                           H       NHCOCH.sub.3                                                                           272.5 nm                              23 CH.sub.3 (CH.sub.2).sub.12                                                                           NHCOCH.sub.3                                                                           H       295.5 nm                              24 CH.sub.3 (CH.sub.2).sub.14                                                                           NHCOCH.sub.3                                                                           H       296 nm                                25 CH.sub.3 (CH.sub.2).sub.14                                                                           H       NHCOCH.sub.3                                                                           136-139                               26 CH.sub.3 (CH.sub.2).sub.16                                                                           H       NHCOCH.sub.3                                                                           127                                   27 CH.sub.3 OCH.sub.2    H       NHCOCH.sub.3                                                                           129-130                               28 CH.sub.3 OCH.sub.2    NHCOCH.sub.3                                                                           H       294 nm                                29 C.sub. 2 H.sub.5 OCH.sub.2                                                                           NHCOCH.sub.3                                                                           H       156-160                               30 C.sub.2 H.sub.5 OCH.sub.2                                                                            H       NHCOCH.sub.3                                                                           276 nm                                31 (CH.sub.3).sub.2 CH   H       NHCOCH.sub.3                                                                           271 nm                                32 (CH.sub.3).sub.2 CH   NHCOCH.sub.3                                                                           H       295 nm                                33 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2                                                                   H       NHCOCH.sub.3                                                                           150                                   34 C.sub.6 H.sub.5       H       NHCOCH.sub.3                                                                           183-185                               35 ClCH.sub.2 CH.sub.2   H       NHCOCH.sub.3                                                                           163                                                                            (decomposition)                       36 CH.sub.3              Cl      Cl      111                                   37                                                                                 ##STR28##            H       NHCOCH.sub.3                                                                           120                                   38 CH.sub.2CH            H       NHCOCH.sub.3                                                                           160-162                                                                        (decomposition)                       39 ClCH.sub.2            H       NHCOCH.sub.3                                                                           185-188                                                                        (decomposition)                       40                                                                                 ##STR29##            H       NHCOCH.sub.3                                                                           220-230                               41 HO.sub.2 CCH.sub.2 CH.sub.2                                                                          H       NHCOCH.sub.3                                                                           270 nm (154)                          42 HO.sub.2 CCH CH       H       NHCOCH.sub.3                                                                           278 nm                                43 ClCH.sub.2 CH.sub.2 CH.sub.2                                                                         H       NHCOCH.sub.3                                                                           273 nm                                44 C.sub.6 H.sub.5 OCH.sub.2                                                                            H       NHCOCH.sub.3                                                                           155                                   __________________________________________________________________________

EXAMPLE 3

144 parts of 4-acetylaminobenzamidoxime are dissolved in 200 parts by volume of N-methylpyrrolidone and 200 parts by volume of acetone, and 90 parts of volume of butyryl chloride are added, 10% strength sodium hydroxide solution being added at the same time so that the pH of the reaction mixture is kept at 4.5-7.0. Stirring is continued for 1 hour at from 25° to 45° C., after which precipitation is effected by dilution with water, and the precipitate is filtered off under suction, washed salt-free with water and dried to give 180 parts of the product of the formula ##STR30##

When the colorless powder is heated at 170° C., water is eliminated to give the product of the formula ##STR31## in the form of a melt which, when it is cooled, solidifies to give a product of melting point 171° C.

This compound is brominated by a conventional method (for example in glacial acetic acid or sulfuric acid at ≦40° C.) to give 1-acetylamino-2-bromo-4-(5-n-propyl-1,2,4-oxadiazol-3-yl)-benzene of the formula ##STR32## (UV spectrum: λ_(max) =268.5 nm in methanol).

41 parts of this product in 200 parts by volume of methanol are stirred with 30 parts of concentrated sulfuric acid, with vapor cooling. After 1 hour, the mixture is neutralized and some of the methanol is then distilled off. The reaction mixture is diluted with water, and the resulting precipitate is filtered off under suction, washed with water and dried to give 33 parts of the diazo component of the formula ##STR33## in the form of a colorless powder of melting point 88°-90° C.

41 parts of 4-(5-n-propyl-1,2,4-oxadiazol-3-yl)aniline in 200 parts by volume of glacial acetic acid and 45 parts of anhydrous sodium acetate are stirred, 80 parts of bromine are added at from 20° to 50° C., stirring is continued for a further 2 hours and the resulting, colorless product of the formula ##STR34## is precipitated with water (λ_(max) =284.5 nm).

The product is filtered off under suction, washed with water and dried to give 69 parts of a colorless powder. If the bromination is carried out in 85-98% sulfuric acid, a smaller amount of bromine is required.

The compounds of the general formula IV which are stated in Table C can be prepared by a procedure similar to that described in the Examples.

                                      TABLE C                                      __________________________________________________________________________      ##STR35##                                      IV                                                                          λ.sub.max. (nm)                                                         or melting                        No.                                                                               R                   X.sup.1                                                                           X  Y       Z       point (°C.)                __________________________________________________________________________     1  CH.sub.3            H  Cl H       NHCOCH.sub.3                                                                           134-136                                                                        (269.0 nm)                        2  CH.sub.3            H  Cl H       NH.sub.2                                                                               283 nm                            3  CH.sub.3            H  H  NH.sub.2                                                                               H       97-98                             4  CH.sub.3            H  Cl Cl      NH.sub.2                                                                               110                                                                            (282.5 nm)                        5  CH.sub.3            H  Br H       NHCOCH.sub.3                                                                           152-155                           6  CH.sub.3            H  Br H       NH.sub.2                                                                               148-150                                                                        (284.0 nm)                        7  CH.sub.3            H  Br Br      NH.sub.2                                                                               160-161                                                                        (283 nm)                          8  CH.sub.3            Br H  NH.sub.2                                                                               Br      289 nm                            9  CH.sub.3            NO.sub.2                                                                          H  NH.sub.2                                                                               H       130-135                           10 CH.sub.3            H  H  NH.sub.2                                                                               NO.sub.2                                                                               98-103                            11 CH.sub.3            H  CH.sub.3                                                                          H       NO.sub.2                                                                               143-145                           12 CH.sub.3            H  CH.sub.3                                                                          H       NH.sub.2                                                                               136-138                           13 CH.sub.3            CH.sub.3                                                                          H  NH.sub.2                                                                               H       322 nm                            14 C.sub.2 H.sub.5     H  H  H       NHCOCH.sub.3                                                                           149-150                           15 C.sub.2 H.sub.5     H  H  Br      NHCOCH.sub.3                                                                           113-114                                                                        (268.5 nm)                        16 C.sub.2 H.sub.5     H  H  Br      NH.sub.2                                                                               65-67                                                                          (248.5 nm)                        17 C.sub.2 H.sub.5     H  H  Cl      NH.sub.2                                                                               283 nm                            18 C.sub.2 H.sub.5     H  Cl Cl      NH.sub.2                                                                               290 nm                            19 C.sub.2 H.sub.5     H  H  Cl      NHCOCH.sub.3                                                                           267 nm                            20 C.sub.2 H.sub.5     H  Br Br      NH.sub.2                                                                               284.5 nm                          21 C.sub.2 H.sub.5     Br H  NHCOCH.sub.3                                                                           Br      160-165                                                                        (290.5 nm)                        22 C.sub.2 H.sub.5     H  H  NH.sub.2                                                                               H       318                                                                            230 nm                            23 C.sub.2 H.sub.5     H  H  NHCOCH.sub.3                                                                           H       302 nm                            24 C.sub.2 H.sub.5     Br H  NH.sub.2                                                                               Br      306 nm                            25 C.sub.2 H.sub.5     H  H  NH.sub.2                                                                               NO.sub.2                                                                               95-99                             26 C.sub.2 H.sub.5     NO.sub.2                                                                          H  NH.sub.2                                                                               H       76-81                             27 n-C.sub.3 H.sub.7   H  H  H       NHCOCH.sub.3                                                                           168-171                           28 n-C.sub.3 H.sub.7   H  Cl H       NHCOCH.sub.3                                                                           267 nm                            29 n-C.sub.3 H.sub.7   H  Cl H       NH.sub.2                                                                               218 and                                                                        283 nm                            30 n-C.sub.3 H.sub.7   H  Cl Cl      NH.sub.2                                                                               283 nm                            31 n-C.sub.3 H.sub.7   H  H  NHCOCH.sub.3                                                                           H       299 nm                            32 n-C.sub.3 H.sub.7   H  H  NH.sub.2                                                                               H       317 and                                                                        229 nm                            33 n-C.sub.3 H.sub.7   H  H  H       NH.sub.2                                                                               88-90                             34 CH.sub.3 OCH.sub.2  H  H  NHCOCH.sub.3                                                                           H       302 nm                            35 CH.sub.3 OCH.sub.2  H  Br H       NHCOCH.sub.3                                                                           79-83                             36 CH.sub.3 OCH.sub.2  H  Br H       H       269 nm                            37 CH.sub.3 OCH.sub.2  H  H  NH.sub.2                                                                               H       316 nm                            38 CH.sub.3 OCH.sub.2  H  Br Br      NH.sub.2                                                                               283 nm                            39 CH.sub.3 OCH.sub.2  H  Cl Cl      NH.sub.2                                                                               282 nm                            40 CH.sub.3 OCH.sub.2  H  H  Cl      NH.sub.2                                                                               218 and                                                                        282 nm                            41 CH.sub.3 OCH.sub.2  H  H  Br      NH.sub.2                                                                               46-49                                                                          286.5 nm                          42 CH.sub.3 OCH.sub.2  H  H  H       NHCHO   276 nm                            43 CH.sub.3 OCH.sub.2  H  H  NHCHO   H       308 nm                            44 (CH.sub.3).sub.3 C  H  Br H       NH.sub.2                                                                               56-58                                                                          284.5 nm                          45 (CH.sub.3).sub.3 C  H  Br Br      NH.sub.2                                                                               87-89                                                                          284.5 nm                          46 CH.sub.3 OCH.sub.2 CH.sub.2                                                                        H  H  NHCOCH.sub.3                                                                           H       294 nm                            47 CH.sub.3 OCH.sub.2 CH.sub.2                                                                        H  H  H       NHCOCH.sub.3                                                                           273 nm                            48 CH.sub.3 OCH.sub.2 CH.sub.2                                                                        H  Br H       NHCOCH.sub.3                                                                           268 nm                            49 CH.sub.3 OCH.sub.2 CH.sub.2                                                                        H  Br Br      NHCOCH.sub.3                                                                           275 nm                            50 (CH.sub.3).sub.2 CH H  H  NHCOCH.sub.3                                                                           H       296 nm                            51 (CH.sub.3).sub.2 CH H  H  H       NHCOCH.sub.3                                                                           275 nm                            52 (CH.sub.3).sub.2 CH H  H  Br      NHCOCH.sub.3                                                                           267.5 nm                          53 (CH.sub.3).sub.2 CH H  H  Br      NH.sub.2                                                                               220 and                                                                        285 nm                            54 (CH.sub.3).sub.2 CH H  H  NH.sub.2                                                                               H       228 and                                                                        318 nm                            55 (CH.sub.3).sub.2 CH H  Br Br      NH.sub.2                                                                               222 and                                                                        285 nm                            56 (CH.sub.3).sub.2 CH H  Cl Cl      NH.sub.2                                                                               221 and                                                                        283 nm                            57 (CH.sub.3).sub.2 CH H  Cl H       NH.sub.2                                                                               286 nm                            58 n-C.sub.4 H.sub.9   H  H  NHCOCH.sub.3                                                                           H       296 nm                            59 n-C.sub.4 H.sub.9   H  H  H       NHCOCH.sub.3                                                                           274 nm                            60 n-C.sub.4 H.sub.9   H  H  H       NH.sub.2                                                                               286 nm                            61 n-C.sub.4 H.sub.9   H  H  Br      NH.sub.2                                                                               288 nm                            62 n-C.sub.4 H.sub.9   H  Br Br      NH.sub.2                                                                               222 and                                                                        284.5 nm                          63 n-C.sub.4 H.sub.9   H  Cl Cl      NH.sub.2                                                                               221 and                                                                        284 nm                            64 (CH.sub.3).sub.3 C  H  H  NHCOCH.sub.3                                                                           H       295 nm                            65 (CH.sub.3).sub.3 C  H  H  H       NHCOCH.sub.3                                                                           173-175                           66 (CH.sub.3).sub.3 C  H  H  Br      NHCOCH.sub.3                                                                           85-87                             67 (CH.sub.3).sub.3 C  H  H  Cl      NHCOCH.sub.3                                                                           220 and                                                                        268 nm                            68 n-C.sub.6 H.sub.13  H  H  NHCOCH.sub.3                                                                           H       231.5 and                                                                      296 nm                            69 n-C.sub.6 H.sub.13  H  H  NH.sub.2                                                                               H       228.5 and                                                                      316 nm                            70 n-C.sub.6 H.sub.13  H  H  H       NHCOCH.sub.3                                                                           273 nm                            71 n-C.sub.6 H.sub.13  H  H  H       NH.sub.2                                                                               284 nm                            72 n-C.sub.6 H.sub.13  H  H  Br      NH.sub.2                                                                               286 nm                            73 n-C.sub.6 H.sub.13  H  H  Br      NHCOCH.sub.3                                                                           287 nm                            74 n-C.sub.6 H.sub.13  H  H  Cl      NHCOCH.sub.3                                                                           268 nm                            75 n-C.sub.6 H.sub.13  H  Br Br      NH.sub.2                                                                               285 nm                            76 n-C.sub.6 H.sub.13  H  Cl Cl      NH.sub.2                                                                               284 nm                            77 n-C.sub.7 H.sub.15  H  Cl Cl      NH.sub.2                                                                               285 nm                            78 n-C.sub.7 H.sub.15  H  H  Cl      NHCOCH.sub.3                                                                           268.5 nm                          79 n-C.sub.7 H.sub.15  H  H  H       NHCOCH.sub.3                                                                           274 nm                            80 n-C.sub.7 H.sub.15  H  H  Br      NHCOCH.sub.3                                                                           276 nm                            81 n-C.sub.7 H.sub.15  H  H  Br      NH.sub.2                                                                               284.5 and                                                                      220 nm                            82 n-C.sub.7 H.sub.15  H  Br Br      NH.sub.2                                                                               285 nm                            83 n-C.sub.7 H.sub.15  H  H  NH.sub.2                                                                               H       316.5 and                                                                      228 nm                            84 n-C.sub.7 H.sub.15  H  H  NHCOCH.sub.3                                                                           H       295 and                                                                        231 nm                            85 n-C.sub.7 H.sub.15  H  H  Cl      NH.sub.2                                                                               285 nm                            86 n-C.sub.7 H.sub.15  H  H  NH.sub.2                                                                               Cl      320 nm                            87                                                                                 ##STR36##          H  Br Br      NH.sub.2                                                                               285 nm                            88                                                                                 ##STR37##          H  H  Br      NH.sub.2                                                                               284 nm                            89                                                                                 ##STR38##          H  H  Cl      NHCOCH.sub.3                                                                           25                                90                                                                                 ##STR39##          H  H  Br      NHCOCH.sub.3                                                                           25                                91                                                                                 ##STR40##          H  H  Br      NH.sub.2                                                                               20                                92                                                                                 ##STR41##          H  H  H       NHCOC.sub.2 H.sub.5                                                                    48-53                             93                                                                                 ##STR42##          H  H  NH.sub.2                                                                               Cl      10-16                             94                                                                                 ##STR43##          H  H  H       NH.sub.2                                                                               38-40                             95 (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                                 H  H  H       H       317 and                                                                        228 nm                            96 (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                                 H  H  NHCOCH.sub.3                                                                           H       296 nm                            97 (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                                 H  H  H       NHCOCH.sub.3                                                                           269 nm                            98 (CH.sub. 3).sub.3 C(CH.sub.2).sub.5                                                                H  H  Br      NHCOCH.sub.3                                                                           268.5 nm                          99 (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                                 H  H  Br      NH.sub.2                                                                               287 nm                            100                                                                               (CH.sub.3).sub.3 C(CH.sub.2).sub.5                                                                 H  Br Br      NH.sub.2                                                                               285 nm                            101                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  Br Br      NH.sub.2                                                                               286 nm                            102                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  H  Br      NH.sub.2                                                                               287 nm                            103                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  H  H       NH.sub.2                                                                               285 nm                            104                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  H  H       NHCOCH.sub.3                                                                           296 nm                            105                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  H  Br      NHCOCH.sub.3                                                                           269 nm                            106                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  Br Br      NH.sub.2                                                                               286 nm                            107                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  H  NHCOCH.sub.3                                                                           H       296.5 nm                          108                                                                               CH.sub.3 (CH.sub.2).sub.10                                                                         H  H  NH.sub.2                                                                               H       319 nm                            109                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  H  NH.sub.2                                                                               H                                         110                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  H  H       NHCOCH.sub.3                                                                           78-85                             111                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  H  H       NH.sub.2                                                                               285.5 nm                                                                       50-60                             112                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  H  Br      NH.sub.2                                                                               286 nm                            113                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  Br Br      NH.sub.2                                                                               287 nm                            114                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  H  Br      NHCOCH.sub.3                                                                           270 nm                            115                                                                               CH.sub.3 (CH.sub.2).sub.14                                                                         H  H  NH.sub.2                                                                               H       320 nm                            116                                                                               C.sub.17 H.sub.35   H  H  H       NHCOCH.sub.3                                                                           80-85                             117                                                                               CH.sub.3 (CH.sub.2).sub.16                                                                         H  H  NH.sub.2                                                                               H       319 nm                            118                                                                               CH.sub.3 (CH.sub.2).sub.16                                                                         H  H  H       NH.sub.2                                                                               286 nm                            119                                                                               CH.sub.3 (CH.sub.2).sub.16                                                                         H  H  Br      NH.sub.2                                                                               287 nm                            120                                                                               CH.sub.3 (CH.sub.2).sub.16                                                                         H  Br Br      NH.sub.2                                                                               288 nm                            121                                                                               CH.sub.3 (CH.sub.2).sub.16                                                                         H  H  Br      NHCOCH.sub.3                                                                           274 nm                            122                                                                                ##STR44##          H  H  H       NHCOCH.sub.3                                                                           250-253                           123                                                                               C.sub.6 H.sub.5     H  H  H       NHCOCH.sub.3                                                                           180-183                           123a                                                                              C.sub.6 H.sub.5     H  H  NHCOCH.sub.3                                                                           H       190-193                           124                                                                               C.sub.6 H.sub.5     H  H  Br      NHCOCH.sub.3                                                                           268.5 nm                          125                                                                               C.sub.6 H.sub.5     H  Br Br      NHCOCH.sub.3                                                                           269 nm                            126                                                                               C.sub.6 H.sub.5     H  Cl Cl      NHCOCH.sub.3                                                                           266 nm                            127                                                                               C.sub.6 H.sub.5     H  Cl Cl      NH.sub.2                                                                               142-145                           128                                                                               C.sub.6 H.sub.5     H  H  Br      NH.sub.2                                                                               289 nm                            129                                                                               C.sub.6 H.sub.5     H  H  Cl      NH.sub.2                                                                               289 nm                            130                                                                               C.sub.6 H.sub.5     H  H  NH.sub.2                                                                               H       320 nm                                                                         143-145                           131                                                                                ##STR45##          H  H  NH.sub.2                                                                               H       317 nm                            132                                                                                ##STR46##          H  H  H       NH.sub.2                                                                               287 nm                            133                                                                                ##STR47##          H  H  H       NHCOCH.sub.3                                                                           275 nm                            134                                                                                ##STR48##          H  H  Br      NHCOCH.sub.3                                                                           268 nm                            135                                                                               C.sub.6 H.sub.5 OCH.sub.2                                                                          H  H  H       NHCOCH.sub.3                                                                           165                                                                            275.0 nm                          135a                                                                              C.sub.6 H.sub.5 OCH.sub.2                                                                          H  NH.sub.2                                                                          H       H       115                               136                                                                               C.sub.6 H.sub.5 OCH.sub.2                                                                          H  H  H       NH.sub.2                                                                               110-112                           137                                                                               C.sub.6 H.sub.5 CH.sub.2 OCH.sub.2                                                                 H  H  H       NH.sub.2                                                                               90-94                             138                                                                               C.sub.6 H.sub.5 CH.sub.2 OCH.sub.2                                                                 H  H  NH.sub.2                                                                               H       318 nm                            139                                                                                ##STR49##          H  H  NH.sub.2                                                                               H       319 nm                            140                                                                                ##STR50##          H  H  H       NH.sub.2                                                                               286 nm                            141                                                                                ##STR51##          H  H  NHCOCH.sub.3                                                                           H       295 nm                            142                                                                                ##STR52##          H  H  NH.sub.2                                                                               H       317 nm                            143                                                                                ##STR53##          H  H  H       NH.sub.2                                                                               283 nm                            144                                                                                ##STR54##          H  H  H       NHCOCH.sub.3                                                                           274 nm                            145                                                                                ##STR55##          H  H  Br      NHCOCH.sub.3                                                                           267 nm                            146                                                                                ##STR56##          H  H  Br      NH.sub.2                                                                               284 nm                            147                                                                                ##STR57##          H  H  Br      NH.sub.2                                                                               269 nm                            148                                                                                ##STR58##          H  H  NH.sub.2                                                                               H       316 nm                            149                                                                                ##STR59##          H  H  NH.sub.2                                                                               H       318 nm                            150                                                                                ##STR60##          H  H  H       NH.sub.2                                                                               284.5 nm                          151                                                                                ##STR61##          H  H  Br      NH.sub.2                                                                               289 nm                            152                                                                               C.sub.6 H.sub.5 CH.sub.2                                                                           H  H  H       NH.sub.2                                                                               285 nm                            153                                                                               C.sub.6 H.sub.5 CH.sub.2                                                                           H  H  NH.sub.2                                                                               H       319 nm                            154                                                                                ##STR62##          H  H  NH.sub.2                                                                               H       319 and 228 nm                    155                                                                                ##STR63##          H  H  H       NH.sub.2                                                                               281 nm                            156                                                                                ##STR64##          H  H  H       NH.sub.2                                                                               103- 105 279.5 nm                 157                                                                                ##STR65##          H  H  H       NHCOCH.sub.3                                                                           183-185 273.5 nm                  158                                                                                ##STR66##          H  H  NH.sub.2                                                                               H       319 and 228 nm                    159                                                                               CH.sub.3            H  H  NH.sub.2                                                                               OCH.sub.3                                                                              325 nm                            160                                                                                ##STR67##          H  H  NH.sub.2                                                                               OCH.sub.3                                                                              325 nm                            161                                                                               CH.sub.3 O.sub.2 CC.sub.2 H.sub.4                                                                  H  H  H       NH.sub.2                                                                               105-107                           162                                                                               HO.sub.2 CC.sub.2 H.sub.4                                                                          H  H  NH.sub.2                                                                               H       318 nm                            163                                                                               HO.sub.2 CC.sub.2 H.sub.4                                                                          H  H  H       NH.sub.2                                                                               284 nm                            164                                                                               HO.sub.2 CC.sub.2 H.sub.4                                                                          H  H  NH.sub.2                                                                               Br      321 nm                            165                                                                               HO.sub.2 CC.sub.2 H.sub.4                                                                          H  H  NHCOCH.sub.3                                                                           H       295.5 nm                          __________________________________________________________________________

EXAMPLE 4

370 parts of the compound of the formula ##STR68## are introduced into 800 g of 96% strength sulfuric acid at from 15° to 20° C., 150 parts by volume of concentrated nitric acid are then added dropwise at from 0° to 10° C., and the mixture is stirred for a further hour at room temperature. When nitration is complete, the mixture is poured onto ice water and stirred until the reaction is complete, and the precipitate is buffered at pH 4.5-7.

The oily phase is separated off, and stirred with about 1,000 parts by volume of methanol. The resulting yellow precipitate is filtered off under suction, washed with methanol and dried to give 100 parts of a product of melting point 143°-146° C., the formula of which is probably ##STR69##

The filtrate contains, in addition to a small amount of this product, an isomer which presumably has the following formula ##STR70## This compound is isolated by evaporating the methanol.

By means of catalytic (or Bechamp) reduction, the nitro compounds are converted to the amines of the formula ##STR71## of melting point 136°-138° C. (or ##STR72## having a melting range from 100° to 135° C., since this product contains a small amount of impurities).

If nitration is carried out using the oxadiazole derivatives of the formulae ##STR73## pure nitro derivatives of the formulae ##STR74## respectively, are obtained, which can be reduced to the corresponding amines in a conventional manner.

The yellow dyes of the general formulae V and VI shown in Tables D and E can be prepared by methods similar to those described.

                  TABLE D                                                          ______________________________________                                          ##STR75##                     V                                                                                         λ.sub.max.                    No.  R            R.sup.1       X    X.sup.1 Y                                                                           (nm)                                 ______________________________________                                               ##STR76##   CH.sub.3      H    H H  438                                  2                                                                                    ##STR77##   C.sub.2 H.sub.5                                                                              H    H H  439.5                                3                                                                                    ##STR78##   n-C.sub.3 H.sub.7                                                                            H    H H  439.5                                4                                                                                    ##STR79##   i-C.sub.3 H.sub.7                                                                            H    H H  439.5                                5                                                                                    ##STR80##   n-C.sub.4 H.sub.9                                                                            H    H H  439.5                                6                                                                                    ##STR81##   i-C.sub.4 H.sub.9                                                                            H    H H  439.5                                7                                                                                    ##STR82##   n-C.sub.6 H.sub.13                                                                           H    H H  439.5                                8    CH.sub.3 (CH.sub.2).sub.6                                                                   CH.sub.3      H    H H  439.5                                9    CH.sub.3 (CH.sub.2).sub.6                                                                   H             H    H H  438                                  10   CH.sub.3 (CH.sub.2).sub.6                                                                   C.sub.2 H.sub.5                                                                              H    H H  439                                  11   CH.sub.3 (CH.sub.2).sub.6                                                                   n-C.sub.3 H.sub.7                                                                            H    H H  439                                  12   CH.sub.3 (CH.sub.2).sub.6                                                                   i-C.sub.3 H.sub.7                                                                            H    H H  439                                  13                                                                                   ##STR83##   CH.sub.3      H    H H  439                                  14                                                                                   ##STR84##   C.sub.2 H.sub.5                                                                              H    H H  439                                  15                                                                                   ##STR85##   n-C.sub.3 H.sub.7                                                                            H    H H  439                                  16                                                                                   ##STR86##   i-C.sub.3 H.sub.7                                                                            H    H H  439                                  17                                                                                   ##STR87##   C.sub.2 H.sub.4 OCH.sub.3                                                                    H    H H  439                                  18                                                                                   ##STR88##   C.sub.3 H.sub.6 OCH.sub.3                                                                    H    H H  439                                  19   C.sub.6 H.sub.5 CH.sub.2 OC.sub.2 H.sub.4                                                   CH.sub.3      H    H H  439.5                                20   HO.sub.2 CC.sub.2 H.sub.4                                                                   H             H    H H  438                                  21   HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OCH.sub.3                                                                    H    H H  438.5                                22   HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                          H    H H  438.5                                23   HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                          H    H H  438.5                                24   HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                   H    H H  438.5                                25   HO.sub.2 CCH.sub.2                                                                          C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                                   H    H H  439                                  26   HO.sub.2 CCH.sub.2                                                                          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                          H    H H  439                                  27                                                                                   ##STR89##   CH.sub.2 CHCH.sub.2                                                                          H    H H  439.5                                28   C.sub.6 H.sub.5 OCH.sub.2                                                                   CH.sub.3      H    H H  439                                  29   C.sub.6 H.sub.5 OCH.sub.2                                                                   C.sub.2 H.sub.5                                                                              H    H H  439                                  30   CH.sub.3     C.sub.2 H.sub.5                                                                              H    H H  437.5                                31   CH.sub.3     CH.sub.3      H    H H  438                                  32   CH.sub.3     H             H    H H  438                                  33   C.sub.2 H.sub.5                                                                             H             H    H H  438                                  34   C.sub.2 H.sub.5                                                                             CH.sub.3      H    H H  438                                  35   C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                              H    H H  439                                  36   C.sub.2 H.sub.5                                                                             n-C.sub.3 H.sub.7                                                                            H    H H  439                                  37   C.sub.2 H.sub.5                                                                             CHCH.sub.2CH.sub.2                                                                           H    H H  440                                  38   n-C.sub.3 H.sub.7                                                                           CH.sub.3      H    H H  439                                  39   n-C.sub.3 H.sub.7                                                                           C.sub.2 H.sub.5                                                                              H    H H  439.5                                40   n-C.sub.3 H.sub.7                                                                           n-C.sub.4 H.sub.9                                                                            H    H H  439.5                                41                                                                                   ##STR90##   H             Br   H H  438                                  42                                                                                   ##STR91##   CH.sub.3      Br   H H  438                                  43                                                                                   ##STR92##   CH.sub.3      Cl   H H  438                                  44                                                                                   ##STR93##   CH.sub.3      NO.sub.2                                                                            H H  447                                  45                                                                                   ##STR94##   H             NO.sub.2                                                                            H H  446                                  46                                                                                   ##STR95##   C.sub.2 H.sub.5                                                                              NO.sub.2                                                                            H H  448                                  ______________________________________                                    

                                      TABLE E                                      __________________________________________________________________________      ##STR96##                            VI                                                                         λ.sub.max.(nm)                                                          or melting                                   No.                                                                               R            R.sup.1 R.sup.2                                                                             Y  X.sup.1                                                                          point (°C.)                           __________________________________________________________________________     1  n-C.sub.3 H.sub.7                                                                           CH.sub.3                                                                               H    NO.sub.2                                                                          H 436 nm                                       2  n-C.sub.3 H.sub.7                                                                           C.sub.2 H.sub.5                                                                        H    NO.sub.2                                                                          H 437 nm                                       3  n-C.sub.3 H.sub.7                                                                           n-C.sub.3 H.sub.7                                                                      H    NO.sub.2                                                                          H 437 nm                                       4  n-C.sub.3 H.sub.7                                                                           n-C.sub.4 H.sub.9                                                                      H    NO.sub.2                                                                          H 437 nm                                       5  n-C.sub.3 H.sub.7                                                                           n-C.sub.6 H.sub.13                                                                     H    NO.sub.2                                                                          H 437 nm                                       6  n-C.sub.7 H.sub.15                                                                          H       H    NO.sub.2                                                                          H 110-116                                      7  n-C.sub.7 H.sub.15                                                                          CH.sub.3                                                                               H    NO.sub.2                                                                          H 103-108                                      8  n-C.sub.7 H.sub.15                                                                          C.sub.2 H.sub.5                                                                        H    NO.sub.2                                                                          H 105-109                                      9  n-C.sub.7 H.sub.15                                                                          n-C.sub.3 H.sub.7                                                                      H    NO.sub.2                                                                          H 100-103                                      10                                                                                 ##STR97##   H       H    NO.sub.2                                                                          H 436 nm                                       11                                                                                 ##STR98##   H       COCH.sub.3                                                                          NO.sub.2                                                                          H 439 nm                                       12                                                                                 ##STR99##   CH.sub.3                                                                               H    NO.sub.2                                                                          H 438 nm                                       13                                                                                 ##STR100##  C.sub.2 H.sub.5                                                                        H    NO.sub.2                                                                          H 438 nm                                       14                                                                                 ##STR101##  n-C.sub.3 H.sub.7                                                                      H    NO.sub.2                                                                          H 438 nm                                       15 n-C.sub.8 H.sub.17                                                                          H       H    NO.sub.2                                                                          H 437 nm                                       16 n-C.sub.8 H.sub.17                                                                          CH.sub.3                                                                               H    NO.sub.2                                                                          H 438 nm                                       17 n-C.sub. 8 H.sub.17                                                                         C.sub.2 H.sub.5                                                                        H    NO.sub.2                                                                          H 438 nm                                       18                                                                                 ##STR102##  H       CN   Br H 429 nm                                       19                                                                                 ##STR103##  H       CN   Cl Cl                                                                               425 nm                                       20                                                                                 ##STR104##  CH.sub.3                                                                               CN   Cl Cl                                                                               426 nm                                       21                                                                                 ##STR105##  CH.sub.3                                                                               CN   Br H 429 nm                                       22                                                                                 ##STR106##  n-C.sub.4 H.sub.9                                                                      CN   Cl Cl                                                                               425 nm                                       23                                                                                 ##STR107##  n-C.sub.4 H.sub.9                                                                      CN   Br Br                                                                               425 nm                                       24 n-C.sub.8 H.sub.17                                                                          CH.sub.2 CH.sub.2 OCH.sub.3                                                            CN   H  H 428 nm                                       25 n-C.sub.8 H.sub.17                                                                          (CH.sub.2).sub.3 OCH.sub.3                                                             CN   H  H 428 nm                                       26 n-C.sub.4 H.sub.9OC.sub.2 H.sub.4                                                           H       CN   H  H 427.5 nm                                     27 n-C.sub.4 H.sub.9 OC.sub.2 H.sub.4                                                          CH.sub.3                                                                               CN   Cl H 428 nm                                       28 n-C.sub.4 H.sub.9OC.sub.2 H.sub.4                                                           CH.sub.3                                                                               H    NO.sub.2                                                                          H 436 nm                                       29 n-C.sub.4 H.sub.9OC.sub.2 H.sub.4                                                           C.sub.2 H.sub.5                                                                        H    NO.sub.2                                                                          H 436 nm                                       30                                                                                 ##STR108##  H       H    NO.sub.2                                                                          H 436 nm                                       31                                                                                 ##STR109##  CH.sub.3                                                                               H    NO.sub.2                                                                          H 437 nm                                       32                                                                                 ##STR110##  H       CN   H  H 427.5 nm                                     33                                                                                 ##STR111##  n-C.sub.3 H.sub.7                                                                      CN   H  H 428.5 nm                                     34                                                                                 ##STR112##  C.sub.2 H.sub.5                                                                        CN   H  H 428.5 nm                                     35                                                                                 ##STR113##  C.sub.2 H.sub.5                                                                        CN   H  H 428.5 nm                                     36                                                                                 ##STR114##  CH.sub.3                                                                               CN   H  H 428.5 nm                                     37                                                                                 ##STR115##  CH.sub.3                                                                               CN   H  H 428.5 nm                                     38                                                                                 ##STR116##  CH.sub.3                                                                               CN   H  H 428.5 nm                                     39 HO.sub.2 CC.sub.2 H.sub.4                                                                   H       CN   H  H 428.5 nm                                     40 HO.sub.2 CC.sub.2 H.sub.4                                                                   H       CONH.sub.2                                                                          H  H 412 nm                                       41 HO.sub.2 CC.sub.2 H.sub.4                                                                   H       H    H  H 410 nm                                       42 HO.sub.2 CC.sub.2 H.sub.4                                                                   CH.sub.3                                                                               H    H  H 410 nm                                       43 HO.sub.2 CC.sub.2 H.sub.4                                                                   CH.sub.3                                                                               CONH.sub.2                                                                          H  H 413 nm                                       44 HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OCH.sub.3                                                              CONH.sub.2                                                                          H  H 413 nm                                       45 HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OCH.sub.3                                                              H    H  H 412 nm                                       46 HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OCH.sub.3                                                              CN   H  H 412 nm                                       47 HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH                                                    CN   H  H 429 nm                                       48 HO.sub.2 CC.sub.2 H.sub.4                                                                   C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                    CN   H  H 429 nm                                       49                                                                                 ##STR117##  H       COCH.sub.3                                                                          H  H 410 nm                                       __________________________________________________________________________

The greenish yellow dyes of the general formula VII which are stated in the Table can be prepared by a procedure similar to that described in the examples.

                                      TABLE F                                      __________________________________________________________________________      ##STR118##                          VII                                                                       λ.sub.max. (nm)                                                         or melting                                     No. R           R.sup.1   X  X.sup.1                                                                           point (°C.)                             __________________________________________________________________________          ##STR119## CH.sub.3  H  H  428 nm                                         2                                                                                   ##STR120## C.sub.2 H.sub.5                                                                          H  H  428.5 nm                                       3                                                                                   ##STR121## n-C.sub.3 H.sub.7                                                                        H  H  428.5 nm                                       4                                                                                   ##STR122## i-C.sub.3 H.sub.7                                                                        H  H  428.5 nm                                       5                                                                                   ##STR123## n-C.sub.4 H.sub.9                                                                        H  H  429 nm                                         6                                                                                   ##STR124## i-C.sub.4 H.sub.9                                                                        H  H  429 nm                                         7                                                                                   ##STR125## n-C.sub.6 H.sub.13                                                                       H  H  429 nm                                         8                                                                                   ##STR126##                                                                                 ##STR127##                                                                              H  H  428 nm                                         9                                                                                   ##STR128## C.sub.2 H.sub.4 OH                                                                       H  H  428 nm                                         10                                                                                  ##STR129## C.sub.3 H.sub.6 OH                                                                       H  H  428 nm                                         11                                                                                  ##STR130## C.sub.6 H.sub.13 OH                                                                      H  H  428 nm                                         12                                                                                  ##STR131## C.sub.2 H.sub.4 OCH.sub.3                                                                H  H  428 nm                                         13                                                                                  ##STR132## C.sub.3 H.sub.6 OCH                                                                      H  H  428 nm                                         14                                                                                  ##STR133## C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                                         H  H  428 nm                                         15                                                                                  ##STR134## C.sub.2 H.sub.4 OC.sub.4 H.sub.9                                                         H  H  428 nm                                         16                                                                                  ##STR135## CH.sub.3  Br H  429 nm                                         17                                                                                  ##STR136## n-C.sub.4 H.sub.9                                                                        Br Br 416 nm                                         18                                                                                  ##STR137## CH.sub.2 CHCH.sub.2                                                                      H  H  429 nm                                         19  n-C.sub.7 H.sub.15                                                                         H         H  H  427 nm                                         20  n-C.sub.7 H.sub.15                                                                         CH.sub.3  H  H  427,5 nm                                                                       131-133                                        21  n-C.sub.7 H.sub.15                                                                         C.sub.2 H.sub.5                                                                          H  H  427.5 nm                                                                       142-145                                        22  n-C.sub.7 H.sub.15                                                                         C.sub.3 H.sub.7                                                                          H  H  427.5 nm                                       23  n-C.sub.6 H.sub.13                                                                         H         H  H  427.5 nm                                       24  n-C.sub.6 H.sub.13                                                                         CH.sub.3  H  H  427.5 nm                                       25  n-C.sub.6 H.sub.13                                                                         C.sub.2 H.sub.5                                                                          H  H  427.5 nm                                       26  n-C.sub.6 H.sub.13                                                                         CH.sub.2 CHCH.sub.2                                                                      H  H  427.5 nm                                       27  n-C.sub.3 H.sub.7                                                                          H         H  H  427 nm                                         28  n-C.sub.3 H.sub.7                                                                          CH.sub.3  H  H  427 nm                                         29  n-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                                          H  H  427 nm                                         30  CH.sub.3    H         H  H  427 nm                                         31  CH.sub.3    CH.sub.3  H  H  427 nm                                         32  CH.sub.3    C.sub.2 H.sub.5                                                                          H  H  427 nm                                                                         228-231                                        33  CH.sub.3    n-C.sub.4 H.sub.9                                                                        H  H  427 nm                                         34  C.sub.6 H.sub.5 OCH.sub.2                                                                  CH(CH.sub.3).sub.2                                                                       H  H  428 nm                                         35  C.sub.6 H.sub.5 OCH.sub.2                                                                  CH.sub.3  H  H  428 nm                                         36  C.sub.6 H.sub.5 OCH.sub.2                                                                  C.sub.2 H.sub.5                                                                          H  H  428 nm                                         37  C.sub.6 H.sub.5 OCH.sub.2                                                                  n-C.sub.3 H.sub.7                                                                        H  H  428 nm                                         38  CH.sub.3 OCH.sub.3                                                                         n-C.sub.3 H.sub.7                                                                        H  H  428 nm                                         39  CH.sub.3 OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                          H  H  428 nm                                         40  CH.sub.3 OCH.sub.3                                                                         i-C.sub.3 H.sub.7                                                                        H  H  428 nm                                         41  CH.sub.3 O.sub.2 CC.sub.2 H.sub.4                                                          C.sub.2 H.sub.5                                                                          H  H  429 nm                                         42  CH.sub.3 O.sub.2 CC.sub.2 H.sub.4                                                          CH.sub.3  H  H  429 nm                                         43  C.sub.2 H.sub.5 O.sub.2 CC.sub.2 H.sub.4                                                   C.sub.2 H.sub.5                                                                          H  H  429 nm                                         44  H.sub.9 C.sub.4 O.sub.2 CC.sub.2 H.sub.4                                                   C.sub.2 H.sub.5                                                                          H  H  429 nm                                         45  H.sub.13 C.sub.6 O.sub.2 CC.sub.2 H.sub.4                                                  C.sub.2 H.sub.5                                                                          H  H  429 nm                                         46  C.sub.4 H.sub.9 O.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4                                   C.sub.2 H.sub.5                                                                          H  H  429 nm                                             H.sub.3O.sub.2                                                             47  CACH.sub.2 O.sub.2 CC.sub.2 H.sub.4                                                        C.sub.2 H.sub.5                                                                          H  H  429 nm                                             H.sub.9 C.sub.4                                                            48                                                                                  ##STR138## C.sub.2 H.sub.5                                                                          H  H  430 nm                                         __________________________________________________________________________

EXAMPLE 5

23.5 parts of the diazo component of the formula ##STR139## are diazotized in a conventional manner, and the resulting diazonium salt solution is run into a very thoroughly stirred solution of 24 parts of the coupling component of the formula ##STR140## in 500 parts of water, 200 parts of ice and 10 parts of sodium carbonate.

The coupling mixture is brought to pH 3.5-4.5, and the precipitated dye of the formula ##STR141## is filtered off under suction and isolated in a conventional manner. Drying of the product gives 46 parts of a yellow powder, which dyes nylon fabrics and leather in greenish yellow hues with good fastness properties.

The yellow dyes of the general formula VIII which are shown in Table G can be obtained by a procedure similar to that described in Example 5.

                                      TABLE G                                      __________________________________________________________________________      ##STR142##                             VIII                                   No. R         R.sup.1  R.sup.2                                                                              X   H  λ.sub.max. (nm)                     __________________________________________________________________________     1   n-C.sub.7 H.sub.15                                                                       H        H     NO.sub.2                                                                           H  435 nm                                     2   n-C.sub.7 H.sub.15                                                                       H        COCH.sub.3                                                                           NO.sub.2                                                                           H  439 nm                                     3   n-C.sub.7 H.sub.15                                                                       CH.sub.3 COCH.sub.3                                                                           NO.sub.2                                                                           H  438 nm                                     4   n-C.sub.7 H.sub.15                                                                       CH.sub.3 H     NO.sub.2                                                                           H  435 nm                                          ##STR143##                                                                              H        H     NO.sub.2                                                                           H  435 nm                                     6                                                                                   ##STR144##                                                                              H        COCH.sub.3                                                                           NO.sub.2                                                                           H  439 nm                                     7                                                                                   ##STR145##                                                                              CH.sub.3 COCH.sub.3                                                                           NO.sub.2                                                                           H  438 nm                                     8                                                                                   ##STR146##                                                                              CH.sub.3 H     NO.sub.2                                                                           H  436 nm                                     9                                                                                   ##STR147##                                                                              H        CN    NO.sub.2                                                                           H  446 nm                                     10                                                                                  ##STR148##                                                                              CH.sub.3 CN    NO.sub.2                                                                           H  447 nm                                     11                                                                                  ##STR149##                                                                              CH.sub.3 CN    Br  H  438 nm                                     12                                                                                  ##STR150##                                                                              H        CN    Br  H  439 nm                                     13                                                                                  ##STR151##                                                                              H        CN    Cl  H  439 nm                                     14                                                                                  ##STR152##                                                                              C.sub.2 H.sub.5                                                                         H     NO.sub.2                                                                           H  437 nm                                     15                                                                                  ##STR153##                                                                              n-C.sub.4 H.sub.9                                                                       H     NO.sub.2                                                                           H  437 nm                                     16  C.sub.6 H.sub.5 OCH.sub.2                                                                C.sub.2 H.sub.5                                                                         CN    H   H  440 nm                                     17  C.sub.6 H.sub.5 OCH.sub.2                                                                CH.sub.3 CN    H   H  440 nm                                     18  n-C.sub.11 H.sub.23                                                                      C.sub.4 H.sub.9                                                                         CN    H   H  440 nm                                     19  n-C.sub.11 H.sub.23                                                                      n-C.sub.6 H.sub.13                                                                      CN    H   H  440 nm                                     20  n-C.sub.11 H.sub.23                                                                      C.sub.3 H.sub.6 OCH.sub.3                                                               CN    H   H  440 nm                                     21                                                                                  ##STR154##                                                                              C.sub.3 H.sub.6 OCH.sub.3                                                               CN    H   H  440 nm                                     22                                                                                  ##STR155##                                                                              n-C.sub.6 H.sub.13                                                                      n-C.sub.6 H.sub.13                                                                   H   H  440 nm                                     23                                                                                  ##STR156##                                                                              C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                     CN    H   H  440 nm                                     24  n-C.sub.11 H.sub.23                                                                      C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                     CN    H   H  440 nm                                     25  n-C.sub.15 H.sub.31                                                                      C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                                     CN    H   H  440 nm                                     26  n-C.sub.15 H.sub.31                                                                      C.sub.3 H.sub.6 OCH.sub.3                                                               CN    H   H  440 nm                                     27  n-C.sub.15 H.sub.31                                                                      n-C.sub.4 H.sub.9                                                                       CN    H   H  440 nm                                     28  HO.sub.2 CC.sub.2 H.sub.4                                                                H        CN    H   H  440 nm                                     29  HO.sub.2 CC.sub.2 H.sub.4                                                                H        CONH.sub.2                                                                           H   H  426 nm                                     30  HO.sub.2 CC.sub.2 H.sub.4                                                                CH.sub.3 CONH.sub.2                                                                           H   H  426 nm                                     31  HO.sub.2 CC.sub.2 H.sub.4                                                                CH.sub.3 CN    H   H  440 nm                                     32  HO.sub.2 CC.sub.2 H.sub.4                                                                CH.sub.3 CONH.sub.2                                                                           Br  H  428 nm                                     33  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.2 H.sub.5                                                                         CONH.sub.2                                                                           Br  H  428 nm                                     34  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.2 H.sub.5                                                                         CONH.sub.2                                                                           H   H  426 nm                                     35  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.2 H.sub.4 OCH.sub.3                                                               CONH.sub.2                                                                           H   H  426 nm                                     36  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.2 H.sub.4 OCH.sub.3                                                               CN    H   H  440 nm                                     37  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.3 H.sub.6 OCH.sub.3                                                               CN    H   H  440 nm                                     38  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.3 H.sub.6 OCH.sub.3                                                               CONH.sub.2                                                                           H   H  426 nm                                     39  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.3 H.sub.6 OCH.sub.3                                                               CONH.sub.2                                                                           Br  H  428 nm                                     40  HO.sub.2 CCHCH                                                                           H        CN    H   H  440 nm                                     41  HO.sub.2 CCHCH                                                                           CH.sub.3 CN    H   H  440 nm                                     42  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.2 H.sub.4 OH                                                                      CN    Br  H  441 nm                                     43  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.3 H.sub.6 OH                                                                      CN    Br  H  440 nm                                     44  HO.sub.2 CC.sub.2 H.sub.4                                                                C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                     CN    H   H  440 nm                                     45  HO.sub.2 CCHCH                                                                           C.sub.3 H.sub.6 OH                                                                      CN    H   H  440 nm                                     46  HO.sub.2 CCHCH                                                                           C.sub.2 H.sub.4 OH                                                                      CN    H   H  440 nm                                     47  HO.sub.2 CCHCH                                                                           C.sub.2 H.sub.4 OCH.sub.3                                                               CN    H   H  440 nm                                     48  HO.sub.2 CCHCH                                                                           C.sub.3 H.sub.6 OCH.sub.3                                                               CN    H   H  440 nm                                     49  HO.sub.2 CCHCH                                                                           C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                     CN    H   H  440 nm                                     50  HO.sub.2 CCH.sub.2                                                                       C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                     CN    H   H  440 nm                                     51  HO.sub.2 CCH.sub.2                                                                       C.sub.2 H.sub.4 OH                                                                      CN    H   H  440 nm                                     52  HO.sub.2 CCH.sub.2                                                                       C.sub.3 H.sub.6 OH                                                                      CN    H   H  440 nm                                     53  HO.sub.2 CCHCH                                                                           C.sub.2 H.sub.4 OCH.sub.3                                                               CONH.sub.2                                                                           H   H  426 nm                                     54  HO.sub.2 CCHCH                                                                           C.sub.3 H.sub.6 OCH.sub.3                                                               CONH.sub.2                                                                           H   H  427 nm                                     55  HO.sub.2 C(CH.sub.2).sub.3                                                               C.sub.3 H.sub.6 OCH.sub.3                                                               CN    H   H  440 nm                                     56  HO.sub.2 C(CH.sub.2).sub.3                                                               C.sub.2 H.sub.4 OH                                                                      CN    H   H  440 nm                                     57  HO.sub.2 C(CH.sub.2).sub.4                                                               C.sub.2 H.sub.4 OH                                                                      CN    H   H  440 nm                                     58  HO.sub.2 C(CH.sub.2).sub.4                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                     CN    H   H  440 nm                                     59  n-C.sub.3 H.sub.7                                                                        CH.sub.3 CN    Br  Br 416 nm                                     60                                                                                  ##STR157##                                                                              H        COCH.sub.3                                                                           H   H  428.5 nm                                   61                                                                                  ##STR158##                                                                              H        COCH.sub.3                                                                           Br  H  428.5 nm                                   62  CH.sub.3 O.sub.2 CC.sub.2 H.sub.4                                                        C.sub.2 H.sub.5                                                                         CN    H   H  439 nm                                     __________________________________________________________________________

The dyes stated in Table H can be prepared by a procedure similar to that described in Examples 9, 10 and 11.

                  TABLE H                                                          ______________________________________                                          ##STR159##                                                                                                                λ.sub.max.                  No.  R.sup.1    R.sup.2  R.sup.3                                                                               R.sup.4                                                                              Hue   (nm)                               ______________________________________                                         1    C.sub.6 H.sub.5                                                                           n-C.sub.13 H.sub.27                                                                     CN     H     yellow                                                                               440                                2    C.sub.6 H.sub.5                                                                           n-C.sub.13 H.sub.27                                                                     CN     Cl    yellow                                                                               442                                3    C.sub.6 H.sub.5                                                                           i-C.sub.8 H.sub.17                                                                      CN     Cl    yellow                                                                               442                                4    C.sub.6 H.sub.5                                                                           i-C.sub.8 H.sub.17                                                                      CN     OCH.sub.3                                                                            yellow                                                                               449                                      ##STR160##                                                                               i-C.sub.8 H.sub.17                                                                      CN     H     yellow                                                                               441                                6    C.sub.3 H.sub.7                                                                           i-C.sub.8 H.sub.17                                                                      CN     H     yellow                                                                               440                                7    C.sub.3 H.sub.7                                                                           i-C.sub.8 H.sub.17                                                                      CN     Cl    yellow                                                                               442                                8    CH.sub.3   n-C.sub.13 H.sub.27                                                                     CONH.sub.2                                                                            H     yellow                                                                               425.5                              9    CH.sub.3   n-C.sub.13 H.sub.27                                                                     CONH.sub.2                                                                            Cl    yellow                                                                               427                                10   CH.sub.3   n-C.sub.12 H.sub.25                                                                     COCH.sub.3                                                                            Cl    yellow                                                                               427.5                              11   CH.sub.3   n-C.sub.12 H.sub.25                                                                     COCH.sub.3                                                                            H     yellow                                                                               427.5                              12                                                                                   ##STR161##                                                                               n-C.sub.4 H.sub.9                                                                       CONH.sub.2                                                                            H     yellow                                                                               426                                13   C.sub.5 H.sub.11                                                                          i-C.sub.8 H.sub.17                                                                      CONH.sub.2                                                                            H     yellow                                                                               426                                ______________________________________                                    

EXAMPLE 6

21 parts of the compound of the formula ##STR162## are stirred thoroughly overnight with 50 parts of a 30% strength hydrochloric acid and 1 part of a dispersant which is effective under acidic conditions. The mixture is then cooled to 0°-5° C., and 32-34 parts of a 23% strength sodium nitrite solution are run in under the surface of the suspension in the course of about 20-30 minutes, the temperature being kept at 0°-5° C. during this procedure by the addition of ice. The diazotization mixture is stirred for a further 2-3 hours at from 0° to 5° C., after which about 150 parts of ice water are added, nitrite is destroyed in a conventional manner and the pH of the diazotization mixture is brought to 0.5-1.0 with a little sodium formate. A solution comprising 23.6 parts of 1-n-hexyl-2-hydroxy-3-cyano-4-methylpyrid-6-one, 300 parts by volume of water and 12 parts of 50% strength sodium hydroxide solution is then run in. Coupling is complete after a few minutes. The precipitated dye is filtered off under suction, washed with water and dried, these steps being carried out in a conventional manner. 45 parts of a yellow powder of the formula ##STR163## are obtained. The product dissolves in dimethylformamide to give a yellow solution, and dyes polyester fabric in very lightfast deep yellow hues.

EXAMPLE 7

24.5 parts of the diazo component of the formula ##STR164## are diazotized with 33 parts of a 44% strength nitrosylsulfuric acid by a procedure similar to that described in Example 1, the mixture is poured onto ice and water and then stirred until the reaction is complete, and a solution of 23.6 parts of 1-n-hexyl-2-hydroxy-3-cyano-4-methylpyrid-6-one in 250 parts of water and 18 parts of 50% strength sodium hydroxide solution, as well as 1 part of a dispersant (based on an ethylene oxide polymer), are added.

When coupling is complete, the mixture is worked up in a conventional manner to give 48.0 parts of the dye of the formula ##STR165## in the form of a yellow powder. This product dissolves in dimethylformamide to give a yellow solution and gives, on polyester fabric, dyeings having good fastness properties.

EXAMPLE 8

26.5 parts of the diazo component of the formula ##STR166## are diazotized with 34 parts of nitrosylsulfuric acid by a procedure similar to that described in Example 1.

The diazonium salt solution is poured onto ice and stirred to complete the reaction, and 1 part of a dispersant which is effective under acidic conditions is added. Excess nitrous acid is destroyed, after which a solution of 26.4 parts of the coupling component 1-(2-ethylhexyl)-2-hydroxy-3-cyano-4-methylpyrid-6-one in 150 parts by volume of dimethylformamide, 0.5 part of a dispersant, 15 parts of 50% strength sodium hydroxide solution and 30 parts of water are run in, while stirring very thoroughly. Stirring is continued for 1-2 hours, after which the pH of the coupling solution is increased to 6-7.5 by the addition of sodium hydroxide solution.

The product is filtered off under suction, washed with water and dried, these steps being carried out in a conventional manner, and 53 parts of the dye of the formula ##STR167## are obtained in the form of a yellow powder. This product dissolves in dimethylformamide to give a yellow solution, and dyes polyester fabric in very lightfast deep hues.

EXAMPLE 9

Using the roller printing method, a cotton fabric is printed with a printing paste which consists of 15 parts of the dye of the formula ##STR168## 110 parts of polyethylene oxide having a molecular weight of 350, 30 parts of oleic acid diethanolamide and 845 parts of a 10% strength alginate thickener. The print is dried at 100° C., and is then fixed by treating it with hot air at 195° C. for 1 minute. Finishing is carried out and a fast, yellow print on a white ground is obtained.

EXAMPLE 10

On a screen printing machine, a polyester/cellulose blend (weight ratio 67:35) is printed with a mixture which consists of 30 parts of the dye of the formula ##STR169## 100 parts of the reaction product of 3 moles of polyethylene oxide of molecular weight 300 with 1 mole of boric acid, 30 parts of oleic acid diethanolamide and 840 parts of a 3% strength alginate thickener. The print is dried at 110° C., and is then treated with steam at 185° C. for 5 minutes. It is finished and a fast, yellow print on a white ground is obtained.

EXAMPLE 11

Using a padding machine, a cotton fabric is padded with a solution which contains 20 parts of the dye of the ##STR170## 300 parts of a 3% strength alginate thickener, 550 parts of water and 130 parts of polyethylene oxide having a molecular weight of 300. The wet pick-up of the fabric should be 80%. The fabric is dried at 100° C., and the dye is fixed by treatment with steam at 190° C. for 5 minutes. The fabric is then rinsed with cold water, and washed at 90° C. in a bath containing 3 parts of the condensation product of a long-chain alcohol with ethylene oxide in 997 parts of water.

A yellow dyeing is obtained.

Instead of a cotton fabric, it is also possible to pad a polyester/cotton blend (weight ratio 67:33) with the solution described. In the resulting yellow dyeing, the two phases are of the same hue. The treatment with steam can also be replaced by fixing with hot air at 195° C. for 2 minutes. 

We claim:
 1. A compound of the formula ##STR171## wherein R is C₃ -C₁₇ -alkyl, or phenoxymethyl, andR² is hydrogen, C₁ -C₆ -alkyl or allyl, wherein R² is not hydrogen if R is phenoxymethyl.
 2. The compound of claim 1, wherein the oxadiazolyl radical is in the m-position. 